79707-12-3

Usage

Uses

Used in Pharmaceutical Industry:
N3-Benzyl-pyridine-2,3-diamine is used as a building block for the synthesis of novel drug candidates for its interesting biological activities, such as anticancer and antiviral properties.
Used in Medicinal Chemistry:
N3-Benzyl-pyridine-2,3-diamine is used as a valuable intermediate for the development of bioactive molecules with potential therapeutic applications.
Used in Material Science:
N3-Benzyl-pyridine-2,3-diamine is used as a versatile intermediate for the preparation of various functionalized compounds in material science.
Used in Organic Synthesis:
N3-Benzyl-pyridine-2,3-diamine is used as a key intermediate for the synthesis of a wide range of organic compounds with diverse applications.

Upstream product

• 63581-31-7 N₃-benzylidenepyridine-2,3-diamine 
• 54231-40-2 2-nitro-3-benzylaminopyridine 
• 452-58-4 2,3-Diaminopyridine 
• 100-52-7 benzaldehyde 
• 848142-03-0 N³-(Phenylmethylene)-2,3-pyridinediamine 
• 20265-37-6 3-methoxy-2-nitropyridine 
• 100-46-9 benzylamine 
• 100-39-0 benzyl bromide 
• 13534-99-1 2-Amino-3-bromopyridine 
• 54231-35-5 3-fuoro-2-nitropyridine 
• 142670-87-9 N-benzyl-N-(2-chloro-3-pyridinyl)amine 
• 52200-48-3 3-bromo-2-chloropyridine 

Downstream Products

• 105942-43-6 1-(Phenylmethyl)-1H-imidazo<4,5-b>pyridine 
• 848142-03-0 N³-(Phenylmethylene)-2,3-pyridinediamine 
• 1415509-00-0 1-benzyl-1H-imidazo[4,5-b]pyridine-2(3H)-thione 
• 1415509-01-1 1-benzyl-2-bromo-1H-imidazo[4,5-b]pyridine 
• 96428-44-3 3-(cyanomethyl)-2-methyl-8-imidazo<1,2-a>pyridine 
• 85332-80-5 3-amino-2-methyl-8-<(phenylmethyl)amino>imidazo<1,2-a>pyridine 
• 110206-50-3 Benzyl-(2-methyl-imidazo[1,2-a]pyridin-8-yl)-amine 
• 1016-93-9 2-phenyl-1H-imidazo<4,5-b>pyridine 
• 79707-13-4 3-(cyanomethyl)-2-methyl-8-<(phenylmethyl)amino>imidazo<1,2-a>pyridine 

Relevant academic research and scientific papers

1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates

Benzimidazoles are common in nature, medicines, and materials. Numerous strategies for preparing 2-arylbenzimidazoles exist. In this work, 1,2-disubstituted benzimidazoles were prepared from various mono- and disubstituted ortho-phenylenediamines (OPD) by iron-catalyzed oxidative coupling. Specifically, O2 and FeCl3·6H2O catalyzed the cross-dehydrogenative coupling and aromatization of diarylmethyl and dialkyl benzimidazole precursors. N,N′-Disubstituted-OPD substrates were significantly more reactive than their N,N-disubstituted isomers, which appears to be relative to their propensity for complexation and charge transfer with Fe3+. The reaction also converted N-monosubstituted OPD substrates to 2-substituted benzimidazoles; however, electron-poor substrates produce 1,2-disubstituted benzimidazoles by intermolecular imino-transfer. Kinetic, reagent, and spectroscopic (UV-vis and EPR) studies suggest a mechanism involving metal-substrate complexation, charge transfer, and aerobic turnover, involving high-valent Fe(IV) intermediates. Overall, comparative strategies for the relatively sustainable and efficient synthesis of 1,2-disubstituted benzimidazoles are demonstrated.

Streamlined Synthesis of Diaminopyridines by Pd-Catalyzed Ammonia Coupling with Deactivated Amino-Chloropyridines

An efficient and cost-effective two-step synthesis of diaminopyridines, fundamental building blocks of biologically active compounds, is reported. The advantages over previously reported routes include cost and wider availability of the bromo-chloropyridine starting materials and the straightforward accessibility to an extended array of diaminopyridine regioisomers. The key enabler of this synthetic strategy is the development of an unprecedented palladium-catalyzed coupling reaction of ammonia with chloropyridines deactivated by the presence of an alkylamino substituent. The coupling reaction was accomplished with very low catalyst loadings under remarkably mild reaction conditions, making the system particularly suitable for both academic and industrial applications. The utility of this methodology is exemplified by the application to the synthesis of highly relevant scaffolds, including the synthetic intermediates of the marketed drugs Ribociclib and Palbociclib.

Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues

In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products in high yields, alkyltrifluoroborates were found to be less reactive. The utilization of tetrabutylammonium acetate was found to play a substantial role in enhancing the reaction rates of the cross-coupling process. Also, a comparative study was performed between boronic acids and potassium organotrifluoroborate salts.

Rapid construction of imidazopyridines from ortho-haloaminopyridines

A practical strategy for the preparation of imidazopyridine derivatives from ortho-haloaminopyridines utilizing a two-step C-N coupling/cyclization reaction sequence has been developed. This procedure provides rapid and efficient access to many medicinally interesting imidazopyridine compounds and related imidazopyrazine/purine heterocycles.

Metal-free TEMPO-promoted C(sp3)-H amination to afford multisubstituted benzimidazoles

An efficient TEMPO-air/cat. TEMPO-O2 oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp3 C-H and free N-H of readily available N1-benzyl/alkyl-1,2-phenylenediamines.

Synthesis and biological evaluation of imidazo[4,5-b]pyridine and 4-heteroaryl-pyrimidine derivatives as anti-cancer agents

A series of N-phenyl-imidazo[4,5-b]pyridin-2-amines, 4-indazolyl-N- phenylpyrimidin-2-amines and N-phenyl-4-pyrazolo[3,4-b]pyridin-pyrimidin-2- amines have been synthesized. Their anti-proliferative activities were tested in HCT-116 human colon carcinoma and MCF-7 breast carcinoma cell lines. Many exhibited potent anti-proliferative and CDK9 inhibitory activities. A lead compound 18b demonstrated the ability to reduce the level of Mcl-1 anti-apoptotic protein, to activate caspase 3/7 and induce cancer cell apoptosis.

Palladium-Catalyzed C,N-Cross coupling reactions of 3-Halo-2-aminopyridines

A simple approach toward N3-substituted-2,3-diaminopyridines is presented, based on Pd-catalyzed C,N-cross coupling. The use of RuPhos- and BrettPhos-precatalysts in combination with LiHMDS allows for C,N-cross coupling reactions of unprotected

Facile, regioselective syntheses of N-alkylated 2,3-diaminopyridines and imidazo[4,5-b]pyridines

Useful strategies are reported for the differentiation and selective synthetic manipulations of amino groups at the 2- and 3-positions of pyridines. It has been found that 2,3-diaminopyridine reacts with aldehydes under reductive amination conditions to g

PREPARATION OF 2-ARYL-SUBSTITUTED IMIDAZOPYRIDINES AND IMIDAZOPYRIDINES

It is proposed that sulfur be used as the oxidizing agent in the synthesis of 2-arylimidazopyridines from o-diaminopyridines and aromatic (heteroaromatic) aldehydes.Benzyl alcohols and benzylpyridinium salts can be used in place of aldehydes. 2-Phenylimid

Antinuclear Agents. 1. Gastric Antisecretory and Cytoprotective Properties of Substituted Imidazopyridines

A novel class of antinuclear agents, the substituted imidazopyridines, is described.The present compounds are not histamine (H2) receptor antagonists nor are they prostaglandin analoques, yet they exhibit both gastric antisecretory and c